Annual Events

Events are a THING again! But, not every event is happening, and some events are taking different shapes than previous years. Visit each event’s website to get the most up-to-date information.

All year long, Middlebury is home to great events planned by local businesses and organizations, many of which are free or low-cost. Outdoor concerts, markets, parades, holidays festivities, a food truck festival…these are all events you can experience for yourself right here in Middlebury every year. Check them out!


Memorial Day Parade
Hosted by the American Legion

Food truck festival featuring live entertainment hosted by Middlebury Underground 

Festival on the Green
A week-long free concert series on the town green

St Stephen’s Peasant Market
The area’s largest flea market and rummage sale

Lion’s Club Auction
Auction and BBQ on the green

BMP Downtown Block Party
A festive party on the closed off streets of Downtown Middlebury

Middlebury New Filmmakers Festival
A four-day event celebrating new filmmakers

BMP Midd Summer Market
A weekly market series on the Triangle Park Plaza featuring live music and local artisans as well as delicious to-go food


Middlebury Car Show and Fall Festival 
An event co-hosted by the BMP and the Addison County Chamber of Commerce

Middlebury Maple Run hosted by the Addison Independent 
Vermont’s Sweetest Half Marathon and Relay

Turkey Trot by Middlebury Parks and Recreation
Scenic 5K and 10K race with awards and giveaways

Trick-or-Treating down Main Street


Lighten Up 
Middlebury celebrates light with a walk with homemade lanterns throughout the town

Very Merry Middlebury
A month-long celebration of the holidays, including Midd Night Strolls with extended evening shopping, tasting and strolling